Trisazodyestuffs



Patented Mar. 9, 1937 UNITED STATES PATENT OFFICE TRISAZODYESTUFFSHeinrich Clingestein,

Cologneon-the-Rhine,

and Eugen Glietenberg and Oskar Goos, Leverkusen-L G.-Werk, Germany,assignors to General Aniline Works, Inc., New York, N. Y., a corporationof Delaware No Drawing. Application December 14, 1933, Serial No.702,424. In Germany December 21,

Claims.

The present invention relates to trisazodyestufis, more particularly itrelates to dyestuffs which may be represented by the probable generalformula:

HO NH:

wherein R stands for the radical of a diazotization component, such asfor the radical of a diazotized amine of the benzene or naphthaleneseries, one :1: stands for a sulfonic acid group and the other :2:stands for a hydrogen atom, wherein the benzene nuclei R1 and R2 maybear substituents, such as alkyl, alkoxy, halogen or the carboxylic acidgroup and wherein the benzene nucleus R3 is substituted in such a mannerthat the coupling only enters in p-position with respect to the hydroxygroup, this being achieved, for

Hols s OgH Our new dyestuffs are in form of their alkali metal saltsgenerally dark powders, dyeing cotton generally greenish to blue toblack shades of good fastness to acids. They are further distinguishedby dyeing the different fibres in mixed fabrics, for example of cotton,wool, silk and artificial silk, the same shades.

The invention is illustrated by the following examples, without beinglimited thereto:

Example 1.-184 kgs. of benzidine are tetrazotized in the usual mannerand coupled in hydrochloric acid solution with 341 kgs. of l-amino-S-hydroxynaphthalene3,6-disulfonic acid. When the coupling is complete,the intermediate product formed is coupled with diazobenzene preparedfrom 93 kgs. of aniline in sodaalkaline solution. When the diazobenzenehas disappeared, an aqueous solution from kgs. of the hydrochloric acidsalt of 6-chloro-3-aminophenol is added. The dyestuff having in its.free state the following formula:

dyes cotton greenish-black shades of excellent fastness to acids.

By substituting the 1-amino-8-hydroxynaphthalene-3,6-disulfonic acid byl-aminO-S-hydroxynaphthalene-4,6-disulfonic acid, there is obtained adyestufi of similar properties, dyeing somewhat more blue shades.

Example 2.By substituting the diazobenzene in the combination of Example1 by the equivalent quantity of diazotized p-sulfanilic acid, there isobtained a dyestuff having in its free state the following formula:

dyeing leather black shades of a remarkable fastness to acids.

Example 3.-By substituting the 6-chloro-3- aminophenol in thecombination of Example 1 by the equivalent quantity of 4-amino-2-cresol(CI-13:1) there is obtained a dyestufi having in its free state thefollowing formula:

HO N H:

HOzS SOsH dyeing cotton somewhat more reddish shades of good fastness toacids and having the Valuable property of dyeing the different fibres inmixed fabrics the same shades.

By substituting the benzidine by the equivalent quantity of4,4'-diamino-3,3 dimethoxydiphenyl or of4,4'-diamino-3,3'-dimethyldiphenyl or of 4,4 -diamino-3 ,3-dichlorodiphenyl or of 4 ,4 -di aminodiphenyl-3,3-dicarboxylicacid orof 4,4-

R--N=N HOsS HO NH:

from the group consisting of hydrogen, an alkyl, an alkoxy, halogen, thenitro group and the carsame shades.

2. Trisazodyestuifs of the general formula:

wherein R. stands for the radical of a diazotized aromatic amine, one:1: stands for a sulfonic acid group and the other 2: stands for ahydrogen atom, wherein Z and Z stand for members selected from the groupconsisting of hydrogen, an alkyl, an alkoxy, halogen, the nitro groupand the carboxylic acid group and wherein Y stands for a member selectedfrom the group consisting. of hydrogen, alkyl, alkoxy and halogen, beingin the form of their alkali metal salts generally dark powders, dyeingcotton generally greenish to blue to black shades of good fastness toacids and dyeing the different fibres in mixed fabrics the same shades.

HQ! 8 S 03H CH1 3. The trisazodyestuff of the following formula:

dyeing cotton more greenish shades of good fastness to acids.

being in form of its alkali metal salts dark powders, dyeing cottongreenish-black shades of excellent fastness to acids.

We claim: 1. Trisazodyestuffs of the general formula:

no NH: NH,

1 Iv 1 HO; z z' Y 2 wherein R'stands for the radical of -a diazotizedaromatic amine, one It stands for a sulfonic acid group and the other a?stands for a hydrogen atom, wherein Z and Z stand for members selected4. The trisazodyestufi of the following formula:

being in form of its alkali metal salts dark powders, dyeing leatherblack shades of good fastness to acids.

2,073,000 3 5 The trisazodyestuff of the following formula:

HO NE; NH

HOxS S 01H H:

being in form of its alkali metal salts dark pow- HEINRICH CLINGESTEIN.

P0 ders, dyeing cotton red shades of good fastness EUGEN GLIETENBERG.

to acids and dyeing the different fibres in mixed OSKAR GOOS. fabricsthe same shades.

